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In the title mol­ecule, C12H9ClFN5, all bond lengths and angles show normal values. The mean planes of the benzene ring and the purine ring system make a dihedral angle of 77.79 (5)°. Inter­molecular N—H...N hydrogen bonds link the mol­ecules into ribbons extending along the [1\overline{1}0] direction. The crystal packing is further stablized by weak C—H...F and C—H...Cl inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009895/cv2016sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009895/cv2016Isup2.hkl
Contains datablock I

CCDC reference: 605033

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.043
  • wR factor = 0.108
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

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Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).

6-(2-Chloro-4-fluorobenzylamino)purine top
Crystal data top
C12H9ClFN5Z = 2
Mr = 277.69F(000) = 284
Triclinic, P1Dx = 1.573 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2544 (6) ÅCell parameters from 3235 reflections
b = 7.3755 (7) Åθ = 1.8–29.7°
c = 11.8649 (11) ŵ = 0.33 mm1
α = 98.108 (8)°T = 105 K
β = 101.603 (7)°Prism, colourless
γ = 105.518 (8)°0.30 × 0.30 × 0.25 mm
V = 586.28 (10) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer
1908 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Enhance (Oxford Diffraction) monochromatorθmax = 25.0°, θmin = 3.5°
Detector resolution: 16.3 pixels mm-1h = 88
rotation method, ω scansk = 87
5335 measured reflectionsl = 1414
2063 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.05P)2 + 0.65P]
where P = (Fo2 + 2Fc2)/3
2063 reflections(Δ/σ)max = 0.002
173 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl0.25911 (8)0.65716 (9)0.62413 (5)0.0348 (2)
F0.1248 (2)0.8330 (2)0.32535 (12)0.0413 (4)
N10.4265 (3)0.4710 (2)0.80081 (15)0.0222 (4)
C20.5627 (3)0.3804 (3)0.81740 (18)0.0238 (5)
H20.52920.25800.76710.029*
N30.7394 (2)0.4360 (3)0.89422 (15)0.0211 (4)
H30.82260.36820.90010.025*0.18 (4)
C40.7727 (3)0.6110 (3)0.96176 (18)0.0196 (4)
C50.6467 (3)0.7231 (3)0.95572 (18)0.0213 (4)
C60.4645 (3)0.6469 (3)0.87106 (18)0.0211 (4)
N60.3306 (2)0.7430 (2)0.85901 (15)0.0204 (4)
H60.36070.85800.90360.024*
N70.7273 (3)0.8937 (2)1.03853 (15)0.0231 (4)
C80.8992 (3)0.8800 (3)1.09268 (19)0.0238 (5)
H80.98990.97671.15580.029*
N90.9349 (3)0.7146 (2)1.04999 (15)0.0207 (4)
H91.04150.68131.07450.025*0.82 (4)
C90.1390 (3)0.6653 (3)0.77577 (18)0.0202 (4)
H9A0.04120.71040.80980.024*
H9B0.09810.52330.76380.024*
C100.1353 (3)0.7214 (3)0.65746 (17)0.0185 (4)
C110.0396 (3)0.7152 (3)0.58047 (19)0.0224 (5)
C120.0470 (3)0.7532 (3)0.46859 (19)0.0274 (5)
H120.16770.74860.41730.033*
C130.1277 (4)0.7977 (3)0.43538 (19)0.0283 (5)
C140.3045 (3)0.8066 (3)0.5066 (2)0.0281 (5)
H140.42250.83710.48060.034*
C150.3062 (3)0.7698 (3)0.61787 (19)0.0247 (5)
H150.42840.77790.66900.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0192 (3)0.0444 (4)0.0395 (4)0.0122 (2)0.0048 (2)0.0035 (3)
F0.0608 (10)0.0380 (8)0.0225 (7)0.0113 (7)0.0068 (7)0.0110 (6)
N10.0209 (9)0.0256 (9)0.0193 (9)0.0073 (7)0.0039 (7)0.0038 (7)
C20.0252 (11)0.0254 (11)0.0199 (10)0.0065 (9)0.0062 (9)0.0036 (9)
N30.0181 (9)0.0268 (9)0.0195 (9)0.0084 (7)0.0036 (7)0.0071 (7)
C40.0198 (10)0.0252 (11)0.0202 (10)0.0114 (8)0.0088 (8)0.0109 (8)
C50.0234 (11)0.0235 (10)0.0196 (10)0.0092 (9)0.0066 (9)0.0070 (8)
C60.0222 (10)0.0260 (11)0.0196 (10)0.0098 (9)0.0084 (8)0.0099 (8)
N60.0193 (9)0.0223 (9)0.0199 (9)0.0105 (7)0.0012 (7)0.0026 (7)
N70.0276 (10)0.0208 (9)0.0218 (9)0.0089 (7)0.0060 (8)0.0049 (7)
C80.0248 (11)0.0234 (11)0.0245 (11)0.0102 (9)0.0043 (9)0.0059 (9)
N90.0206 (9)0.0225 (9)0.0220 (9)0.0113 (7)0.0044 (7)0.0062 (7)
C90.0175 (10)0.0211 (10)0.0230 (11)0.0068 (8)0.0060 (8)0.0041 (8)
C100.0202 (10)0.0136 (9)0.0205 (10)0.0062 (8)0.0034 (8)0.0001 (8)
C110.0212 (11)0.0181 (10)0.0258 (11)0.0077 (8)0.0021 (9)0.0004 (8)
C120.0338 (13)0.0199 (11)0.0240 (11)0.0116 (9)0.0048 (9)0.0002 (9)
C130.0456 (14)0.0175 (10)0.0202 (11)0.0080 (10)0.0068 (10)0.0043 (8)
C140.0306 (12)0.0247 (11)0.0266 (12)0.0027 (9)0.0099 (10)0.0050 (9)
C150.0212 (11)0.0261 (11)0.0249 (11)0.0059 (9)0.0038 (9)0.0047 (9)
Geometric parameters (Å, º) top
Cl—C111.737 (2)C8—N91.364 (3)
F—C131.364 (3)C8—H80.9500
N1—C21.332 (3)N9—H90.8800
N1—C61.366 (3)C9—C101.516 (3)
C2—N31.336 (3)C9—H9A0.9900
C2—H20.9500C9—H9B0.9900
N3—C41.353 (3)C10—C151.389 (3)
N3—H30.8800C10—C111.392 (3)
C4—N91.365 (3)C11—C121.389 (3)
C4—C51.386 (3)C12—C131.373 (3)
C5—N71.385 (3)C12—H120.9500
C5—C61.407 (3)C13—C141.366 (3)
C6—N61.344 (3)C14—C151.383 (3)
N6—C91.449 (3)C14—H140.9500
N6—H60.8800C15—H150.9500
N7—C81.320 (3)
C2—N1—C6118.16 (18)C4—N9—H9126.8
N1—C2—N3129.6 (2)N6—C9—C10113.70 (17)
N1—C2—H2115.2N6—C9—H9A108.8
N3—C2—H2115.2C10—C9—H9A108.8
C2—N3—C4110.65 (18)N6—C9—H9B108.8
C2—N3—H3124.7C10—C9—H9B108.8
C4—N3—H3124.7H9A—C9—H9B107.7
N3—C4—N9128.00 (18)C15—C10—C11116.84 (19)
N3—C4—C5126.74 (19)C15—C10—C9121.03 (18)
N9—C4—C5105.26 (18)C11—C10—C9122.01 (18)
N7—C5—C4111.41 (19)C12—C11—C10122.6 (2)
N7—C5—C6131.81 (19)C12—C11—Cl117.92 (17)
C4—C5—C6116.77 (19)C10—C11—Cl119.49 (17)
N6—C6—N1120.48 (19)C13—C12—C11117.1 (2)
N6—C6—C5121.48 (19)C13—C12—H12121.5
N1—C6—C5118.03 (18)C11—C12—H12121.5
C6—N6—C9122.76 (18)F—C13—C14118.2 (2)
C6—N6—H6118.6F—C13—C12118.5 (2)
C9—N6—H6118.6C14—C13—C12123.3 (2)
C8—N7—C5102.89 (17)C13—C14—C15117.9 (2)
N7—C8—N9114.00 (19)C13—C14—H14121.0
N7—C8—H8123.0C15—C14—H14121.0
N9—C8—H8123.0C14—C15—C10122.3 (2)
C8—N9—C4106.43 (17)C14—C15—H15118.9
C8—N9—H9126.8C10—C15—H15118.9
C6—N1—C2—N30.7 (3)N7—C8—N9—C40.7 (2)
N1—C2—N3—C40.2 (3)N3—C4—N9—C8179.3 (2)
C2—N3—C4—N9179.58 (19)C5—C4—N9—C80.4 (2)
C2—N3—C4—C50.1 (3)C6—N6—C9—C1092.3 (2)
N3—C4—C5—N7179.61 (18)N6—C9—C10—C1525.0 (3)
N9—C4—C5—N70.1 (2)N6—C9—C10—C11159.18 (18)
N3—C4—C5—C60.4 (3)C15—C10—C11—C120.6 (3)
N9—C4—C5—C6179.36 (18)C9—C10—C11—C12175.38 (18)
C2—N1—C6—N6179.03 (19)C15—C10—C11—Cl179.61 (15)
C2—N1—C6—C50.9 (3)C9—C10—C11—Cl4.4 (3)
N7—C5—C6—N60.1 (3)C10—C11—C12—C130.2 (3)
C4—C5—C6—N6179.16 (19)Cl—C11—C12—C13179.61 (16)
N7—C5—C6—N1179.8 (2)C11—C12—C13—F179.07 (18)
C4—C5—C6—N10.8 (3)C11—C12—C13—C140.3 (3)
N1—C6—N6—C92.3 (3)F—C13—C14—C15179.73 (19)
C5—C6—N6—C9177.61 (18)C12—C13—C14—C150.4 (3)
C4—C5—N7—C80.3 (2)C13—C14—C15—C101.2 (3)
C6—C5—N7—C8178.8 (2)C11—C10—C15—C141.3 (3)
C5—N7—C8—N90.6 (2)C9—C10—C15—C14174.72 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N9i0.882.022.870 (2)163
N6—H6···N7ii0.882.162.953 (2)149
N9—H9···N3i0.882.002.870 (2)170
C8—H8···Fiii0.952.553.029 (3)112
C15—H15···Cliv0.952.773.459 (2)131
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y+2, z+2; (iii) x+1, y, z+1; (iv) x+1, y, z.
 

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